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Jackson, born in Emerson, North Carolina, is the youngest of three children. Stonewall is not a nickname; he was named after the ConfederateGen. Thomas "Stonewall" Jackson. Some publicity for the singer claimed he was a descendant of the general, although this is extremely unlikely. (General Jackson's only descendants are through his daughter Julia's marriage to William Edmund Christian, and these descendants consequently do not bear the surname "Jackson".)

Stonewall's father died when he was two and his mother moved the family to South Georgia. Jackson grew up there working on his uncle's farm. Jackson enlisted in the Navy in 1950 and was discharged in 1954. He moved to Nashville, Tennessee in 1956.

His breakthrough came in the country Top 40 in late 1958, with a song written by a young George Jones, "Life to Go". It peaked at No. 2 in early 1959 and his follow-up record, "Waterloo", was No. 1 for five weeks and crossed over into the Top 40 of the Billboard Hot 100chart, where it reached No. 4. The track also reached No. 24 in the UK Singles Chart in July 1959.[2] It sold over one million copies, and was awarded a gold disc.[3] The song was a haunting and catchy tune that states "Everybody has to meet his Waterloo", meaning their fate. The song cites Adam, Napoleon and Tom Dooley as examples.

His next No. 1 hit came in 1964, with "B.J. the D.J." (about an over-worked country music radio stationdisc jockey, who crashes his car in a rainstorm because of bad tires). In 1963, Jackson was the first artist to record a live album from the Grand Ole Opry with Old Showboat. Other songs of his include "The Carpet On The Floor", "Why I'm Walkin'", "A Wound Time Can't Erase" and "I Washed My Hands in Muddy Water". Jackson also recorded a cover version of Lobo's 1971 hit, "Me and You and a Dog Named Boo".

In 2006, Jackson sued the Grand Ole Opry for $10 million in compensatory damages and $10 million in punitive damage, claiming age discrimination. As a member of the Opry for over fifty years, Jackson believed that management was sidelining him in favor of younger artists. In his court filing, Jackson claimed that Opry general manager Pete Fisher stated that he did not "want any gray hairs on that stage or in the audience, and before I'm done there won't be any." Fisher is also alleged to have told Jackson that he was "too old and too country."[4] The lawsuit was settled on October 3, 2008 for an undisclosed amount and Jackson returned to performing on the show.[5] He has been a member of the Opry since 1956.[1][6]

Jackson lives on a farm in Brentwood, Tennessee with his wife Juanita, who is also his personal manager and operates his song publishing company, Turp Tunes. He has a son, Stonewall Jackson, Jr.